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A9855

3-Acetyl-11-keto-β-boswellic acid

Name: 3-Acetyl-11-keto-β-boswellic acid
Brand: SIGMA

from Boswellia serrata

Synonym(s):

AKBA

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About This Item

Empirical Formula (Hill Notation):

C₃₂H₄₈O₅

CAS Number:

67416-61-9

Molecular Weight:

512.72

MDL number:

MFCD03788777

UNSPSC Code:

12352106

NACRES:

NA.25

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biological source

Boswellia serrata

Quality Level

200

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

O([C@H]1[C@]([C@H]2[C@@]([C@@H]3[C@]([C@@]4(CC[C@@]5([C@@H]([C@H]([C@@H](CC5)C)C)C4=CC3=O)C)C)(CC2)C)(CC1)C)(C)C(=O)O)C(=O)C

InChI

1S/C32H48O5/c1-18-9-12-28(4)15-16-30(6)21(25(28)19(18)2)17-22(34)26-29(5)13-11-24(37-20(3)33)32(8,27(35)36)23(29)10-14-31(26,30)7/h17-19,23-26H,9-16H2,1-8H3,(H,35,36)/t18-,19+,23-,24-,25+,26-,28-,29+,30-,31-,32-/m1/s1

InChI key

HMMGKOVEOFBCAU-BCDBGHSCSA-N

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Related Categories

Biochemicals

Natural Products for Research and Discovery

Chemistry & Biochemicals

General description

Acetyl-11-keto-β-boswellic acid (AKBA) is extracted from the resin of Boswellia serrata.

Application

3-Acetyl-11-keto-β-boswellic acid (AKBA) has been used:

to test its effects as an anti-proliferating agent on hepatic stellate cells (HSCs) proliferation and synergism in combination with imatinib in in vitro models
to study its anti-osteoporotic activity on ovariectomy-induced osteoporosis in female Sprague Dawley rats
in a comparative study with aspirin to test its effects as an anti-inflammatory drug to prevent intestinal adenomatous polyposis in APC^Min/+ mice

Biochem/physiol Actions

Acetyl-11-keto-β-boswellic acid (AKBA) displays antibacterial and anti-biofilm activities against Staphylococcus epidermidis and S. aureus, respectively. It is an activator of nuclear factor erythroid-2-related factor 2 (Nrf2) and exerts neuroprotective properties against ischemic injury in both in vitro and in vivo studies.

Acetyl-11-keto-beta-boswellic acid is a pentacyclic triterpene that inhibits 5-lipoxygenase in a selective, enzyme-directed, nonredox, and noncompetitive manner. It has also been shown to inhibit topoisomerase I and NF-κB signaling.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Antistaphylococcal and biofilm inhibitory activities of acetyl-11-keto-β-boswellic acid from Boswellia serrata.

Alsaba F Raja et al.

BMC microbiology, 11, 54-54 (2011-03-17)

Boswellic acids are pentacyclic triterpenes, which are produced in plants belonging to the genus Boswellia. Boswellic acids appear in the resin exudates of the plant and it makes up 25-35% of the resin. β-boswellic acid, 11-keto-β-boswellic acid and acetyl-11-keto-β-boswellic acid

The Beneficial Effect of Boswellic Acid on Bone Metabolism and Possible Mechanisms of Action in Experimental Osteoporosis.

Bandar E Al-Dhubiab et al.

Nutrients, 12(10) (2020-10-22)

Estrogen is instrumental in the pathological process of osteoporosis because a deficiency of this hormone increases the release of bone-resorbing cytokines. Acetyl-11-keto-β-boswellic acid (AKBA), a constituent from Boswellia serrata, has an anti-inflammatory effect by inhibiting tumor necrosis factor-α (TNF-α) expression

The comparative study of acetyl-11-keto-beta-boswellic acid (AKBA) and aspirin in the prevention of intestinal adenomatous polyposis in APC(Min/+) mice.

Ruiqi Wang et al.

Drug discoveries & therapeutics, 8(1), 25-32 (2014-03-22)

Acetyl-11-keto-beta-BA (AKBA), a component of the gum resin of Boswellia serrata, has been recognized as a promising agent for the prevention of intestinal tumorigenesis. Aspirin, a non-steroidal anti-inflammatory drug (NSAID), has also been considered to have the activity against intestinal

The tyrosine phosphatase SHP-1 inhibits proliferation of activated hepatic stellate cells by impairing PDGF receptor signaling.

Elena Tibaldi et al.

Biochimica et biophysica acta, 1843(2), 288-298 (2013-10-22)

The dimerization and auto-transphosphorylation of platelet-derived growth factor receptor (PDGFR) upon engagement by platelet-derived growth factor (PDGF) activates signals promoting the mitogenic response of hepatic stellate cells (HSCs) due to liver injury, thus contributing to the development of hepatic fibrosis.

Boswellia serrata: an overall assessment of in vitro, preclinical, pharmacokinetic and clinical data.

Mona Abdel-Tawab et al.

Clinical pharmacokinetics, 50(6), 349-369 (2011-05-11)

Non-steroidal anti-inflammatory drug (NSAID) intake is associated with high prevalence of gastrointestinal or cardiovascular adverse effects. All efforts to develop NSAIDs that spare the gastrointestinal tract and the cardiovasculature are still far from achieving a breakthrough. In the last two

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Global Trade Item Number

SKU	GTIN
A9855-5MG	04061832860831

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